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Tandem Iridium-Catalyzed Decarbonylative C-H Activation of Indole: Sacrificial Electron-Rich Ketone-Assisted Bis-arylsulfenylation
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. (Linnaeus Ctr Biomat Chem, BMC;BBCL)ORCID iD: 0000-0003-0774-2528
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. (Linnaeus Ctr Biomat Chem, BMC;BBCL)ORCID iD: 0000-0003-1981-4533
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. (Linnaeus Ctr Biomat Chem, BMC;BBCL)
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Linnaeus University, Linnaeus Knowledge Environments, Advanced Materials. (Linnaeus Ctr Biomat Chem, BMC;BBCL)ORCID iD: 0000-0002-0407-6542
2021 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 23, no 9, p. 3331-3336Article in journal (Refereed) Published
Abstract [en]

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp*IrCl2](2)) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2021. Vol. 23, no 9, p. 3331-3336
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-104505DOI: 10.1021/acs.orglett.1c00829ISI: 000649477300020PubMedID: 33908788Scopus ID: 2-s2.0-85106511554Local ID: 2021OAI: oai:DiVA.org:lnu-104505DiVA, id: diva2:1564432
Available from: 2021-06-11 Created: 2021-06-11 Last updated: 2023-01-23Bibliographically approved
In thesis
1. Novel strategies for C-C/X bond formation
Open this publication in new window or tab >>Novel strategies for C-C/X bond formation
2022 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The formation of C-C/X bonds is essential for the manufacture of a broad range of chemicals and materials used in areas critical for maintaining quality of life in modern society, e.g. pharmaceuticals, agrochemicals and polymers, and for aspects of research in organic chemistry. The use of catalysts for facilitating these reactions is highly desirable due to the improvements in energy and atom economies that can potentially be achieved.The primary objective of the thesis was to explore novel approaches for catalysis of C-C/X bond-forming reactions, both through C-H activation. In paper I, at unable cobalt catalyzed C-H activation-driven annulation of benzamides with unsymmetrical diynes was developed, where either 3- or 4-substitution of the isoquinolone could be steered by the nature of the diyne used. Anunprecedented iridium catalyzed tandem bis-arylsulfenylation of indoles was described (paper II), where an adamantoyl sacrificial directing group plays a key role in the simultaneous direction of arylsulfenylation to the 2- and 4- positions. In paper III, a flow reactor in a lab-on-a-chip device was developed for the Suzuki cross-coupling reaction. Miniaturization provides the opportunity to reduce material consumption. Polyethyleneimine (PEI)-brushes were used for the immobilization of Pd-nanoparticles, and high efficiencies were observed. Collectively, the research underpinning this thesis provides new strategies forC-C and C-X(S) bond formation.

Place, publisher, year, edition, pages
Linnaeus University Press, 2022. p. 70
Series
Linnaeus University Dissertations ; 470
Keywords
annulation, C-H activation, heterocycles, heterogeneous catalysis, homogeneous catalysis, lab-on-a-chip, Suzuki cross-coupling
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-118648 (URN)10.15626/LUD.470.2022 (DOI)9789189709621 (ISBN)9789189709638 (ISBN)
Public defence
2022-11-18, Azur, Hus Vita, Kalmar, 09:30 (English)
Opponent
Supervisors
Available from: 2023-01-23 Created: 2023-01-23 Last updated: 2024-03-07Bibliographically approved

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Kathiravan, SuppanAnaspure, PrasadNicholls, Ian A.

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